(4-Bromo-2-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone → (R)-[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl][2-fluoro-4-(4-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanone

HRID 2411403Notes

Reaction equation

HRID 2411403 reaction equation
[CH3:1][C@H:2]1[CH2:6][S:5](=[O:8])(=[O:7])[NH:4][CH2:3]1.Br[C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[CH:26][N:25]=3)[CH2:20][CH2:19]2)=[O:17])=[C:12]([F:32])[CH:11]=1>>[CH3:30][C:29]1[C:24]([N:21]2[CH2:22][CH2:23][N:18]([C:16]([C:13]3[CH:14]=[CH:15][C:10]([N:4]4[CH2:3][C@@H:2]([CH3:1])[CH2:6][S:5]4(=[O:8])=[O:7])=[CH:11][C:12]=3[F:32])=[O:17])[CH2:19][CH2:20]2)=[N:25][CH:26]=[C:27]([CH3:31])[CH:28]=1

Participants

3

Reactant 2

HCID 58484626(4-Bromo-2-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanoneHCID 86676775(R)-4-methylisothiazolidine 1,1-dioxide

Product 1

HCID 71252723(R)-[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl][2-fluoro-4-(4-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanoneYield 12.6%

Procedure

Using (R)-4-methylisothiazolidine 1,1-dioxide (320 mg) described in Preparation Example 7 and (4-bromo-2-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (439 mg) described in Preparation Example 114 and by the reaction and treatment in the same manner as in Example 1, the title compound (63 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 114 and by the reaction and treatment in the same manner as in Example 1

Sources & evidence

ORD record
ord-fd7dccd9d830493fbec4f76766203317
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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